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Stop Wondering What Questions To Ask When Hiring a VP Marketing/ CMO

CEOs and investors often don't understand the nuts and bolts of marketing. It means when interviewing; it becomes a sort of "unknown unknown". To help on that front, I have collated a set of questions you should be asking.


  • What are the top 3 things we should upgrade in marketing?
  • What “commit” did you hold in your last roles?  How much of it did you meet?
  • How have you worked with the sales team in the past?
  • What should our marketing budget be?
  • How big a team do we need?  
  • What have you done to increase win rates?
  • What should we do to market to each of our top 3 segments?
  • What agencies would you bring in to help us?
  • How much should we focus on building up brand and product awareness?
  • What sort of customer marketing should we do?


  • How did the culture at your last company empower or disempower you?
  • What were the characteristics of the best boss you’ve ever had?
  • Describe how you’ve had a conflict with a co-worker.
  • What kind of feedback do you expect in this role, and how often do you expect it


  • What type of metrics did you use to measure your performance?
  • Pretend you have a funnel showing 10,000 website visitors, 500 leads, 50 opportunities, and ten new enterprise customers. What are the levers or things you suggest to improve those marketing metrics?
  • Keeping it high level, can you describe the lead management process at your current company; how did you model the marketing funnel, what are its different stages, and how is the handoff to the sales team (field, inside sales, SDR etc.)?
  • What’s the conversion rate from marketing/automated generated lead to opportunity/sales qualified lead? And where in your marketing funnel do you think there is an opportunity for improvement?
  • Do you measure your marketing sourced pipeline? If so, how much of the marketing team generates a month, and what per cent of the sales pipeline does this represent?
  • How much time does it take, on average, for a marketing-qualified lead to convert into an opportunity or sales-qualified lead? How do you work with the sales team and inside sales team? How compliant are they with the SLA? What feedback do they have on the process?
  • What’s your cost per opportunity?
  • What do you think about campaigns? What’s your framework for developing campaigns? What are some of the main/overarching campaigns running currently at your company?
  • Can you describe your marketing campaign planning process?
  • How is your team at your current company organised, and why?
  • How do you build your marketing budget and allocate your marketing mix?
  • What are your target customer segments?
  • How do you set goals for yourself, your team, and team members, and what do these goals look like?


Whenever you're ready, there are three ways I can help you:

(1) DUE DILIGENCE FOR INVESTORS & CEOs: A bespoke framework and capability model 'DEMAND KARMA' that delivers DD services to investors, VC firms and CEOs.

(2) ADVISORY: Retained advisory at funded scale-ups. A simple monthly fee. Helping CEOs build a scalable marketing machine. (Booked out until December)

(3) STRATEGY COACHING: Book time on my calendar to work through a standalone project or to get answers to your most pressing marketing strategy and execution questions.

If you're interested, let's jump on a call to see if you're a good fit.

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